IMO, the primary focus of that regulation is to prevent the use of tokens and chips as "legal tender" as a substitute for money. I've seen signs in casino coffee shops & gift stores re not accepting tokens as money.

I know the gaming regulators & the Treasury Dept. would take a dim view of someone trying to buy a used car (or anything) with a rack(s) of chips.

Transferring chips from person A (who won them) to person B (for cashing them in) is frowned upon, if the casino knows about the transfer. Potential problems include money laundering, gambling by minors, etc. Remember the issues with Stupak's "chocolate" chips at the Horseshoe? (though he eventually cashed them)

Casinos clearly have no claim on old/obsolete chips that are still outstanding after being called in for redemption after the notice period has expired. However, I have wondered about the exact "property rights" status of an older chip (say an early Caesars chip) which is still cashable for face value, but worth much more in a dealer's binder on the convention borse. While the casino can't compel the holder to cash it in, I also don't know if the dealer/seller holds absolute & unambiguous title to the chip with rights to offer it for sale. (Sorta like having a car without the pink slip?) This is probably trivial on most chip transactions, but strictly speaking, I think a bill of sale written for a "rare" $100 2nd issue Caesars, selling for $2000 does not constitute a completely clear right of ownership to the buyer.

(On the other hand, I'm not staying awake at night worrying about this either.)